A thread about Oboro looking at his whole backstory, the psychology behind him and his parallelism to Gintoki which makes him one of my all time fav antagonists
(Please excuse me for my bad english)

Oboro has an introduction as an emotional villain, with a special connection to Gintoki. Oboro was the one who forced Gintoki to kill his master which creates instantly hate towards him. His backstory in the end of the Rakuyou Arc recontextualize everything though.

As a young boy, everyone Oboro knew were killed by the Naraku. There was only this one person Shoyo who rescued the little Oboro (who was near death) with a bit of his eternal blood. Therefore Oboro swore to dedicate his whole life into protecting Shoyo.

Oboro encouraged Shoyo to educate, so Oboro was his first pupil. In the end Naraku found them and Oboro gave his own life so that Shoyo could escape. Shoyo escaped as he propably believed his blood wasn‘t enough for Oboros rebirth,

while Oboro choose to be part of Naraku so that he could lead them away from Shoyo.

When Oboro found the Shouka Sonjuku as a coincidence and saw how Shoyo is teaching now other pupils, Oboro was shocked. Deep in his heart I think he wanted to be part of the group and a disciple of Shoyo aswell.

Anyways Oboro was overcome by the feeling that he was excluded. In his eyes he he wasn‘t part of Shoyos school anymore. Therefore he developed egoistic feelings of jealousy towards the disciples of Shoyo and this jealousy lead to two things:

1.His revenge on Shoyo‘s disciples: He forced Gintoki to kill his Master while Takasugi and Zura were forced to watch how their master gets killed by their friend.
2.His egoistic emotion that he claims Shoyo and his teachings only for himself.

It is tragic and really sad because apparently he just wanted to be part of Shoyo‘s school, but his misinterpretation lead to hatred towards Shoyo‘s new disciples. This is extremely interesting and kinda logical from a psychological view which makes Oboro moralicaly grey imo.

Oboro took his revenge and got Shoyo for himself, but the person who got revived wasn’t Shoyo. It was a man filled with pure hate: Utsuro.
Oboro noticed his mistake, but couldn’t betray his master again because of guilt as he was the one who took everything away from Shoyo

Therefore Oboro followed his philosophy to protect Shoyo. But in contrast to Gintoki who focussed on carrying the soul of Shoyo, Oboro has chosen to protect Shoyo‘s body which meant serving Utsuro.

And therefore his backstory fulfilled its purpose to explain and recontextualize the way Oboro acts.

In the Rakuyou Arc Oboro lost to Takasugi.
In his last moment Oboro opened himself to Takasugi and told him everything.
All the time Oboro just wanted to be Shoyo‘s disciple alongside the others, but his misinterpretation and jealousy were reason to Oboro‘s crazy path.

I heard some takes that Oboro redemption was unnecessary.
But the thing is: There wasn’t any redemption. He just made mistakes and chose a wrong path out of guilt. But in his final moments, Oboro’s wish being a member of Shouka Sonjuku was accepted by Takasugi.

Therefore Oboro died in a bittersweet, but heartwarming and meaningful way. A perfect ending.

So that was Oboro‘s character explained, but the final reason which makes him perfect as an antagonist is his parallelism and contrast with Gintoki:
-Obviously similar design (silver hair)
-Gintoki being presented as the first

member of Shouka Sonjuku, while Oboro was the real first member

-Their titles: White Demon vs Messenger from the heaven (contrast)
-Gintoki protecting the soul of Shoyo while Oboro was protecting the physical body of Shoyo (contrast)

-Gin enjoyed learning alongside Takasugi, Zura etc. from Shoyo while Oboro was once overcome by an egoistic wish of claiming Shoyo only for himself

Okay, now that I‘m done, I hope you can appreciate Oboro as an antagonist more now.
Thanks for reading up to this point!